This week, Billboard is publishing a series of lists and articles celebrating the music of 20 years ago. Our 2006 Week continues here with a collection of stories from people who knew Taylor Swift during her first year on the music scene.

Wise beyond her years. Smart as a whip. An extraordinary talent.

When you ask industry insiders who crossed paths with Taylor Swift back in 2006 – the year she released her self-titled debut album – many of the same phrases come up again and again. All of them are descriptors you’d generally expect to hear of the person who, in 20 years, would be the biggest artist in the world, and all of them are traits she’s continued to exhibit over time not only as an experienced musician but as a person.

What’s more striking than the ways she’s remained exactly the same since then, however, are the ways that, two decades ago, Swift was just like any other teenage girl.

For instance? “Taylor did not know how to peel shrimp,” country radio coach John Shomby tells Billboard, laughing fondly at the memory of meeting her for the first time in 2006.

It had been the evening before Swift was slated to play for listeners of WGH-FM, which Shomby oversaw at the time as Max Media’s operations manager, and she and her fledgling team at label Big Machine had requested to go out to dinner with him at Bubba’s in Virginia Beach. Shomby remembers a driven young artist who asked endless questions, was forthright about her ambition to have a No. 1 song someday and — aside from some concern that her parents selling their Christmas tree farm back home to support her pursuit of a music career in Nashville might end up in vain — was strikingly confident, self-assured and accomplished. There was seemingly nothing she couldn’t do.

Until the server set her food down at the table.

“She thought the shrimp was gonna be these little round things that you get in Pennsylvania, where she grew up, at TGI Fridays or something like that,” Shomby says, smiling. “Then they walked in with this big plate of shrimp that were the size of her hand.”

He mimes how her famous blue eyes widened at the sight. “She went, ‘Oh, my. How do you eat these things?’”

Shomby’s wife, Marilyn, went about teaching Swift which parts of the shrimp to peel, eat and avoid, and just like that, the cuisine was the latest of many challenges she had conquered. The next day, she would play debut single “Tim McGraw” for Shomby’s team at the station, and afterward, when he told her that the performance had convinced the team to add the song to their on-air rotations, Shomby says: “You’d think we gave her a million dollars.”

This was how Swift spent much of her first year out – traveling the country, meeting different radio executives and, if she was lucky, getting them to play her music. Oftentimes, she succeeded. If the quality of her early songs didn’t win people over, her natural charm usually did. And if not, she didn’t react with any trace of embarrassment or self-doubt – it was simply on to the next.

That’s how Big Machine’s former west coast promoter Rick Barker, who became Swift’s manager for two years after she signed to the label and accompanied her on those radio visits, remembers it.

“She didn’t know any better,” he says, citing one time when they’d planned a big visit to a station and ordered several pizzas for the occasion, just for three people to show up. “You would have thought there were 300. She went up, shook hands, looked them in the eyes and played her heart out in the conference room.”

“She would just always say things like, ‘Do you think they like me? Do you think they’re gonna add my record?’” Barker continues, remembering how their downtime between tour-bus strategy meetings was filled with talk of Swift’s crushes, MySpace posts and Grey’s Anatomy DVD marathons. “I said, ‘Taylor, I’ll [always] be 100% honest with you, as long as you show me you can handle it. If not, I’ll just blow smoke … and tell you how good you are. She goes, ‘No, I want to know. I want to know what I can do better.’”

Swift was also down to try anything. WGN Radio 720’s Lisa Dent, who conducted one of the singer’s very first major radio interviews in 2006 while working at Chicago’s WUSN, says Swift had no hesitations about spending all day on the air speaking unscripted to countless listeners (most of whom likely had no idea who she was), or about taking a microphone out to Michigan Avenue and asking strangers whether they were Cubs or Sox fans for a segment of the broadcast.

“She’s always been fearless,” Dent says incredulously, inadvertently referencing the title of Swift’s massively successful 2008 sophomore record. “She engages people, and she does that by listening intently – even at that age, you would feel like you were the only person in the room when she made eye contact [with you]. That’s just a part of her DNA.”

Audacy vp of country programming Tim Roberts, who met Swift when she stopped through Detroit on her radio tour, has similar memories. Again, her team had asked to meet for dinner – this time dining at P.F. Changs – and again, she requested to play her music for on-air consideration. Perplexed, Roberts offered to ask the waitstaff if they had a CD player they could borrow.

“She goes, ‘No, I want to play you the songs on my guitar,” he recalls. “Let’s just go out to the parking lot, and I’ll sit in the back of your truck.’”

Outside, she ran through “Tim McGraw” and two other tracks that would become singles from her debut album: “Teardrops on My Guitar” and “Should’ve Said No.” When she was done, Swift – snapping back into teen-girl mode, so to speak – requested to see 8 Mile, the famous namesake and setting of one of her favorite movies she couldn’t stop gushing about over dinner. (Later, when opening for Rascal Flatts in Detroit, she’d play an acoustic-guitar cover of leading man Eminem’s “Lose Yourself.”)

Roberts obligingly took Swift to visit the stretch of road, and “after she left,
I looked at my wife, and I go, ‘Every song she played to me sounded like a No. 1 hit. Maybe it’s just because we spent so much time with her.’ And my wife’s like, ‘No, absolutely. They’re all No. 1s.’”

They were almost right. The first two tracks Swift played would reach No. 2 on the Hot Country Songs chart, after which “Should’ve Said No” became one of Swift’s nine No. 1s on the chart to date.

It’s hard not to notice how certain parts of these memories foreshadow future hallmarks of Swift’s career. In Roberts’ story, she didn’t have a stage on which to perform – so she made her own, evidently spotting his truck at some point before dinner and remembering it later that evening to create an essential opportunity using only what she had at her disposal. That’s not so surprising for someone who would later turn her inability to buy back her own masters into a billion-dollar profit through a series of “Taylor’s Version” releases and her historic Eras Tour.

Then there’s Shomby’s anecdote from the seafood restaurant, which included how “all these guys started looking over” at the tall, blonde and traditionally beautiful young girl he’d walked in with, “but she was completely oblivious.” Instead, she was solely focused on making a good impression with the radio executives – a symbolic counter to how the public would later label her “boy crazy” in dismissal of her talent, meanwhile her career was always the real love of her life (a title fiancé Travis Kelce now shares, of course).

And in Dent’s tale, Swift, after finishing for the day at the Chicago station, taught the radio personality how to take one of those newfangled “selfies.” “That was the first time I’d seen that done,” Dent says, chuckling. “There had to be somebody else in the room, but she took control and said, ‘No, let’s do this.’ It was, I think, an early sign of her controlling her image.”

There are also specific calling cards linking each story. Every person, for instance, volunteers – all unprompted – that 16-year-old Swift followed up each visit with a handwritten thank-you note. (For Dent, Swift went to a nearby stationary store, bought supplies and created a custom piece of colored-pencil art that she then personally delivered to WUSN the next day.) Everyone also remarked on Swift’s “scary good” memory, with Shomby saying, “She knows everybody’s name and everybody’s wife or husband’s name, and their kids.”

“When she played here at Nissan Stadium [in 2019], a bunch of us were backstage,” he continues. “She comes, we’re getting ready to take a picture, and she looks over, and there’s a bowl of shrimp over there. She looks at me and goes, ‘This is kind of ironic, isn’t it?’”

And of course, there’s Andrea. In the periphery of each story from Shomby, Barker, Dent and Roberts, a calm, supportive figure is present in the form of Taylor’s mother, who accompanied her daughter on every step of the radio tour and on most of her journey after that. She served as a constant, protective force (at one point drawing the line that Taylor must wear a coat if she was going to insist on signing autographs for fans lined up in a snowstorm in Utah, Barker remembers). But she also always let the younger Swift take the reins.

“You could tell that she wasn’t, like, a momager,” says Shomby. “Taylor did her thing. Taylor was Taylor.”

At the heart of all these stories is an almost supernaturally determined young girl that was both ravenous for success and deeply interested in forging real connections with the people who could help make that happen. As her star has risen and exploded over time, many have been unable – or unwilling – to reconcile one with the other. She’s been called calculated, manipulative, disingenuous.

But ask the people who knew her from the start, and they’ll tell you something different.

“When she would start winning awards, and people would mock her facial expression or her surprise, it really offended me,” says Dent, whose now-adult son Liam has an autographed poster from Swift – one of his earliest playmates from times spent backstage with her after that initial radio visit – calling him her “favorite boy.” “That was not fake. It wasn’t put on. That was genuine surprise and gratitude.”

Roberts stresses that Swift wasn’t just kind in the moment – she also always remembered who’d helped her and found ways to pay it forward. A few years after meeting at P.F. Changs, she played Palace of Auburn Hills on her Fearless Tour, where a member of her team found Roberts in the crowd mid-show and escorted his party to the end of the stage. Moments later, his face was on the big screens.

“[She] says, ‘This is the song I started my career with, and these people are 100% responsible for me being what I am today,’” Roberts recalls her saying before launching into “Tim McGraw.”

There are also those who attempt to explain away Swift’s success by pointing to her upper-class upbringing or her uber-supportive parents. While certainly helpful, those things are infinitesimal in the long run, argues Barker. After he left his management post with Swift to spend more time with his family – later funneling his experience with her into his book, Music Business for Parents – he started consulting for Sony, where he really got to see, by contrast, just how rare Swift was at 16.

“All these oil dads from Texas were showing up with a blank check and a teenage daughter, thinking that was the magic secret,” he says. “If it were that easy, there would have been a thousand Taylor Swifts.”

Taemin is making history a long way from home. SHINee member and K-pop star appeared on the Wednesday (April 1) episode of The Jennifer Hudson Show, where he spoke about being part of this year’s Coachella lineup.

“You’re making history as the first K-pop male solo artist to perform at Coachella,” Hudson points out during their chat. “How does that feel?”

“There is a saying in Korea, ‘Big opportunities come three times in life,’” Taemin responds after sharing that he was feeling “honored and grateful” to be performing at the festival. “And this is one of them.”

Hudson continues the chat by asking the star if he will release more solo music.

“Oh, yes,” Taemin replies. “I am still evolving.”

The star was also on the talk show to perform his new single, “Long Way Home.” The “Idol’s Idol” sang alone on the stage, dancing effortlessly with his rhinestone microphone and mic stand for the adoring audience.

Performing at Coachella isn’t the only history Taemin is making this year. Billboard exclusively revealed in March that the Grammy Museum in Los Angeles will open a new exhibit dedicated to the K-pop star’s nearly two-decade long career, making him the first K-pop soloist to receive such recognition from the museum. “TAEMIN: Performer. Artist. Icon” will opens April 1 and will give fans a peek behind the curtains of Taemin’s career. Multiple performance looks — including one from his Ephemeral Gaze World Tour — will be on display as well as his official lightstick and a handwritten note addressed to his fans. The special exhibit will run through May 25.

Watch Taemin’s performance and chat on The Jennifer Hudson Show above.

Since 2007, Golnar Khosrowshahi, founder and CEO of Reservoir, has been buying music rights. “It was the not hot, darkest days of the music business,” she says of the time she was setting up the company, referencing challenges with piracy and uncertainty around streaming as a future consumption model for music. “We certainly saw it as an opportunity, but it was not like I had some crystal ball where [I thought] in 15 years, that two, three, four times multiple you’re paying today is going to translate to a 20 times multiple,” she adds with a laugh.

Nearly two decades later, the catalog market is unrecognizable from the one Khosrowshahi entered in 2007. Now, financial players of all types have become keen to buy and flip catalogs. Hipgnosis has driven prices sky high and many artists, sensing the gold rush, have jumped at the chance to cash in. With an early lead on the market, Khosrowshahi’s Reservoir has cemented itself as a competitive player in catalog acquisition, purchasing or administering rights from iconic artists like Miles Davis, Joni Mitchell, De La Soul, Hans Zimmer, Sheryl Crow, Snoop Dogg and more.

On the latest episode of On the Record, Billboard’s music industry podcast, Khosrowshahi details where the catalog market is in 2026, how it got there and her fears of how shifting listening habits among fans could impact the value of hit songs in the future.

Watch or listen to the full episode of On the Record below on YouTube, or check it out on other podcast platforms here.

The conventional wisdom is that the most valuable type of asset is an older, classic rock catalog. And so you see those types of bands and acts fetching really high prices — hundreds of millions, sometimes. But then, on the other hand, I’ve also heard that it’s more difficult, if you’re a country artist, a dance artist, a hip-hop artist, to sell your catalog for those same eye-watering numbers. Can you explain why that is?

Khosrowshahi: I don’t know if I would say it’s difficulties. I think if I were really to break it down, I would say: How widespread is the listenership of the music, and how long is that going to last? How long is this music going to strike a chord with somebody? And really, what that gets you to is: At what rate is the revenue on this music going to decay? Is it here forever? Is it “Take Me Home, Country Roads” that you will keep listening to, and you will be in a situation like we are today, where there are hundreds of covers and user-generated content? Or is it not going to stay with us forever?

Some hits don’t stick around...

Khrosrowshahi: Some hits are great, and they are hits in the moment, and they could be a culturally defining moment, but that doesn’t mean that they will sustain that cultural impact two decades from now…

Also, I think lyrics have a lot to do with it. It’s got to be conducive to film and TV. We see quite a bit of sync licensing across the genres. I think that if the music is at a certain caliber, you are going to get all the licensing opportunities. But in looking at how we value something, we are going to be less optimistic on film and TV sync if we’re looking at music that is filled with expletives. That’s not going to be easy.

Do you think that so many musical biopics are being made right now as a result of some of these top tier catalogs changing hands, and the new owners wanting to exploit the music?

Khosrowshahi: I think it’s partly that, but these stories are interesting, and people like to see interesting stories. Right now, I don’t know about you, but you can’t look anywhere without seeing something about [the biopic] Love Story, [about John F. Kennedy Jr. and Carolyn Bessette]… I think these are just attractive stories to tell… I also think there is just more liquidity and budgets, because the business has grown and that enables either rights holders or filmmakers or adjacent music companies to underwrite these projects. I think that’s why you’re seeing more of these projects come to life.

Reservoir acquired rights to the De La Soul catalog, and then the next month, David from De La Soul passed away. I’m wondering how you handle sensitive times like that. You’ve just spent all this money to acquire this catalog, you’re excited about it, but you also don’t want to be disrespectful or push too hard during a time of mourning. How did you handle that?

Khosrowshahi: It was a very, very difficult time. Outside of just the human, emotional aspect of it — somebody has passed away far too soon — we were three weeks shy, or two weeks shy, of releasing the music. And personally, what made me the most sad at the time was that they wouldn’t enjoy this moment together, the three of them, with their families. Forget about buying the catalog or paying them. That was not a part of what we were thinking. It was that this was going to be such an important moment for them to enjoy, the three of them together.

We went to Times Square with Maseo and Pos, where over the course of that day, I believe we had six or seven billboards, just to be with them and with family and enjoy that moment. It would have been great if he had been there to enjoy that, to see what he meant to people. So it was devastating.

As we know, artists can be unpredictable, and sometimes artists damage their own legacy. When you’re dealing with artists who are still alive and there’s a scandal that takes place — I think of someone like Kanye West or d4vd as examples — how can that impact the value of the catalog?

Khosrowshahi: We haven’t had a lot of drama, but people go through life. We’re in business with people, and people get divorced, and people have hiccups.

Maybe I’m not supposed to say this, but we do look at deals and we do say, ‘Okay, are these people we want to be in business with?’ The scenario that you are painting, we think about that, and there are deals that have transacted that we don’t want to be a part of, because that’s not necessarily a client that we would be the right partner for.

We’re using “artists” and “songwriter” interchangeably here though. Songwriters — a lot of them, you wouldn’t even know by name. Any changes that happen with them is not really a public event. For the most part, I would say that life happens to people, and we’re in business with these songwriters, and things ebb and flow. On the artist side, we’ve been kept safe from notoriety in that we don’t really have that notoriety on the artist roster. I think we’ve just been really lucky… It just hasn’t come up yet. We’ve been pretty protected on that front.

The biggest catalog sale of the last few years was Queen’s sale to Sony Music Publishing. Reportedly, that was over a billion dollars. I imagine there’s a very finite number of artists who can get anywhere close to a billion. With the speed of how many deals are happening, is there a time when we kind of run out of the very, very top-tier catalogs that are on the market?

Khosrowshahi: I worry about that all the time. And I worry about, at what point is a catalog that is 30, 40, 50 years old — at what point does it just transition out of cultural mainstream? At what point is it just no longer relevant? Are we listening to the music from the ’20s or ’30s? Like, name an artist from the ’20s.

I think that’s fair. I also think recording technology was not very good until probably about the ’40s, ’50s. Maybe the ’60s onward — or even ’50s with Elvis — that’s where the evergreen popular music canon really starts.

Khosrowshahi: I do think about what you’re saying a lot — we also have shorter attention spans. We also have much more music that we are exposed to. We have much more choice. We have much more ease with which we can listen to music and find music. So are we listening to our tried-and-true artists on repeat the way we used to, even though we’re listening to more musical hours per week? I would be surprised if you told me that we were listening to the same concentration and not to a more diverse concentration.

Lupe Fiasco is heading to the Acura Grand Prix. While the Chicago native won’t be racing around the Long Beach, Calif., track, Lupe’s slated to headline the Friday Night Concert on April 17 to kick off the high-speed weekend.

“I’ve always been a fan of racing and car culture, so I’m happy to be a part of the Acura Grand Prix of Long Beach,” Lupe Fiasco relayed in a statement.

Fiasco will be bringing his array of hits and lyrical dexterity to the stage, which will serve as a warm-up for the rapper’s Food & Liquor 20th Anniversary Tour kicking off in May.

The Grand Prix show will take place outside the Long Beach Terrace Theater and be free for guests who are ticketholders for April 17.

Tickets are available with general admission day passes starting at $58. Children who are 12 and under will be admitted free with a ticket-holding adult. Lupe’s slated to hit the stage around 6:30 p.m. local time.

“We’re thrilled to welcome Lupe Fiasco to the Acura Grand Prix of Long Beach for our Friday Concert Presented by Acura,” Jim Liaw, who serves as the president and CEO of the Grand Prix Association of Long Beach, said in a statement. “He’s an extraordinary artist with a dynamic stage presence, and this performance will be an exciting way for fans to finish off a great day of racing, entertainment and the Long Beach lifestyle.”

The weekend’s racing action along the Long Beach Waterfront will be headlined by the NTT INDYCAR SERIES and the IMSA WeatherTech SportsCar Championship.

Fiasco’s Food & Liquor 20th Anniversary Tour will kick off on May 14 in Sacramento, Calif., and travel down the state’s coast. He’s also slated for back-to-back shows on June 10 and 11 in NYC and Chicago.